1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 150488
• Molecular Formular: C9H11FN2O4
• Molecular Mass: 230.1930432
• Monoisotopic Mass: 230.07028506
• SMILES: c1cn(c(=O)[nH]c1=O)[C@H]1C[C@@H]([C@H](O1)CO)F
• Canonical SMILES: OC[C@H]1O[C@H](C[C@@H]1F)n1ccc(=O)[nH]c1=O
• InChI: InChI=1S/C9H11FN2O4/c10-5-3-8(16-6(5)4-13)12-2-1-7(14)11-9(12)15/h1-2,5-6,8,13H,3-4H2,(H,11,14,15)/t5-,6+,8+/m0/s1
• InChIKey: BKIUEHLYJFLWPK-SHYZEUOFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]-3H-pyrimidine-2,4-dione
• Synonyms: 3′-Fluoro-2′,3′-dideoxyuridine; 2′,3′-Dideoxy-3′-fluorouridine; 3′-氟-2′,3′-二脱氧尿苷; 2′,3′-二脱氧-3′-氟尿苷

Database IDs

• CAS Number: 41107-56-6
• EC Number: 415-360-8
• MDL Number: MFCD00192015
• Beilstein Number: 6064366
• PubChem SID: 24864537; 24862819; 162244649
• PubChem CID: 162450

CALCULATED PROPERTIES

• Acid pKa: 9.45574
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.62355983
• LogD (pH = 7.4): -0.6272719
• Log P: -0.6235123
• Molar Refractivity: 49.3628 cm^3
• Polarizability: 19.351562 Å^3
• Polar Surface Area: 78.87 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 184-188 °C(lit.)
• Optical Rotation: [α]20/D +10.5±1.0°, c = 1% in 0.5 M NaOH; [α]20/D +10.5°, c = 0.5 in 1 M NaOH

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 68
• Safety Statements: 22-36/37
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H341
• GHS Precautionary statements: P281
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves

Product Information

• Purity: ≥90% (HPLC); 95%
• Grade: technical
• Empirical Formula (Hill Notation): C9H11FN2O4

DETAILS

Sigma Aldrich - 393711

Packaging
25, 100 mg in glass bottle

Sigma Aldrich - 36768

Other Notes
Exhibits anti-retrovirus activity1